


Never Even Been Kissed

by DeansDirtyLittleSecret



Category: Supernatural
Genre: F/M, First Everything, First Time, Originally Posted on Tumblr, Reader-Insert, Smut, Supernatural smut
Language: English
Status: Completed
Published: 2015-07-10
Updated: 2015-07-10
Packaged: 2018-04-08 14:10:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,984
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4308075
Author URL: https://archiveofourown.org/users/DeansDirtyLittleSecret/pseuds/DeansDirtyLittleSecret
Summary: <blockquote class="userstuff">
              <p>Reader lives with the boys and does research for them while they're on hunts. She's kind of quiet and when Dean finds out that she's never even been kissed he shows her how. He's super slow and gentle. Then it leads to them making love. (request on tumblr)</p>
            </blockquote>





	Never Even Been Kissed

“Y/N?” you heard the deep, gravelly voice as it echoed through the bunker, followed by the hollow thunk of the metal door at the top of the stairs.

“I’m in here,” you yelled from the library where you sat surrounded by books. You sat forward in your chair so you could see the Winchester brothers as they came down the stairs, Dean leading the way. He shucked his jacket as he walked, tossing it on the table as he crossed the room. Sam dropped into a chair across from you and began picking up the various books spread across the table, whistling as he silently read some of the titles.

“Wow, Y/N, heavy reading,” he chuckled.  

“Yeah, well, you’re lucky you’ve got me to do all this research for you,” you snapped. “Trust me, I am not enjoying this topic.”

“Is that the stuff on incubi and succubi?” Dean asked, coming up behind you. He leaned over you, his arms on either side of your chair and looked over your shoulder at the book you had in your lap.

You nodded, barely able to concentrate due to the hunter hovering over you. Dean always made you nervous, he was so confident and cocky, always had an opinion and he was never afraid to voice it. Not to mention, he was gorgeous. Really gorgeous. You, on the other hand, were more reserved and quiet, not necessarily shy, but you did prefer books and reading to people sometimes.

“Why is she researching that?” Sam asked Dean.

“I asked her to,” Dean answered, shrugging. “I caught wind of a case in Iowa that might possibly be one of those things. Since we don’t know much about them, I had Y/N look into it for me.”

Sam rolled his eyes. “We’re leaving again?” he grumbled. “We just got back.” He pushed himself out of his chair. “I’m not going anywhere until I shower and sleep for a few hours.” He stalked off, mumbling under his breath the whole time.

“I’m gonna shower too, Y/N, but I’ll be back in a little while,” Dean said. “I want to know what you’ve found.” He disappeared down the hallway.

You returned to your research, jotting down notes as you thumbed through the book in front of you. You felt so awkward researching sex demons, especially when you had never done so much as kissed a guy in your life. Some of the descriptions were very graphic and very embarrassing. You could feel heat flooding your cheeks as you read.

It wasn’t long before Dean returned, clad in a t-shirt and plaid pajama pants, his hair still slightly damp from his shower. He poured himself a drink before sitting in the chair right next to you. He pulled it closer so he could look at the notes you were scribbling. He was so close that his leg  was brushing against yours. He pushed your notebook back to you, but he left his leg where it was.

You glanced at him, but he was sipping his drink and flipping the pages of one of the books on the table. It drove you nuts that he had no idea how he affected you. He seemed completely oblivious to the fact that you trembled every time he put his hand on the small of your back, or that you got goose bumps when he casually hugged you. Every time he touched you, it just made you fall a little harder for him.

You shook yourself free of your thoughts and went back to work. After a few minutes, you seemed to fall into a groove, reading and taking notes, until you stumbled on a particularly graphic description of an incubus and its victim. Reading what the incubus had done to the woman was making you blush furiously, especially with Dean sitting so close to you. For some reason, you kept picturing you and him doing the things you were reading about.  You finally slammed the book shut and pushed it away.

Dean looked up at the sound of the book being closed. “What’s wrong?” he asked.

“Nothing,” you replied, refusing to meet his eyes.

"Seriously, Y/N, just tell me what's wrong," he insisted.

"It's just...well, some of this is embarrassing to read," you explained. "Especially when you've never...well, done...stuff."

"What do you mean by stuff?" he asked.

You stared at the table in front of you, praying it would magically open up and swallow you so you wouldn't have to answer Dean's question. You ran your finger back and forth over a scar marring the wood tabletop, looking at anything but the green eyed hunter.

"Y/N," he said. "What are you talking about?"

"You know, like, sex and stuff," you finally said. You could feel your face burning from the heated blush moving through your body. It wasn't that you were embarrassed that you were a virgin, it was just that Dean was really experienced and he probably thought you were, too. You'd always acted like you were, but now he knew the truth.

Dean looked confused and then his eyes widened slightly, before he forced the look of surprise from his face. "Oh," he murmured. "Umm, okay." He ran his hands through his short hair several times, making it stick up.

You rolled your eyes. "It's not that big of a deal, Dean. I'm sure there are thousands of people out there who've never been kissed."

"Wait a minute," Dean cut you off. "You've never even been kissed? How is that even possible?”

“What do you mean, how is that possible?” you snapped. “I’ve never kissed a guy, okay? Maybe they’ve all been egotistical jerks who think it’s weird that I’ve never been kissed so I won’t kiss them.” You looked pointedly at Dean.

He put his hands in the air, a sheepish grin on his face. “Sorry, sorry,” he muttered. “I’m just surprised because you’re so pretty and sweet and I can’t believe no one’s ever wanted to kiss you.”

“Oh,” you said quietly. Your heart was racing. Had Dean really just said you were pretty and sweet? You stared at your lap, not sure what to say.

Dean’s chair scraped on the floor as he turned it to face you, then he was turning yours so that you were face to face, knees touching. He leaned forward and took your chin in his hand, gently pulling your chin up until you were looking at him.

“Can I kiss you, Y/N?” he asked.

You were pretty sure your heart was going to pound right out of your chest, it was beating so hard. You weren’t sure what was happening, but you weren’t about to say no. You nodded slowly, staring into Dean’s brilliant green eyes.

He gave a gentle tug on your chin, silently urging you to move toward him. You slid to the edge of your seat, meeting Dean halfway and then his perfect, full, pink lips were brushing across yours. You figured that would be the end of it, that Dean would get to brag about being your first kiss, but instead he wrapped an arm around your back, his rough, calloused hands brushing the skin between the waistband of your pajama shorts and your t-shirt, and then his tongue was licking across your bottom lip. You tentatively opened your mouth a tiny bit and then his tongue was delicately running over yours, seemingly begging you to let him in all the way. You opened your mouth further and then Dean was fully exploring your mouth, his tongue moving over your teeth and your lips, his nose brushing against yours as the kiss deepened. One of your hands came up and wrapped around his neck, your fingers brushing over the short hairs there.

The kiss was over far too soon. Dean pulled away, a slight grin on his face. “There, now you’ve been kissed,” he whispered.

You smiled, suddenly embarrassed. “Was I terrible at it?” you asked.

“No,” he chuckled. “In fact, I think with practice, you could get pretty good at it.” He brushed his thumb over your cheek gently as he stared into your (y/e/c) eyes. “If you ever need someone to practice with, I’ll gladly volunteer,” he added, his eyes twinkling.

The idea of kissing Dean some more sent a tingle down your spine. “I’d love that,” you whispered. “A lot.”

Dean’s grin widened.  “Y/N, do you want to practice now?” he prodded.

You closed your eyes and you knew you were blushing furiously, but you finally managed to nod your head. You heard a sharp intake of breath from Dean and then his lips were moving over yours again, his fingers threading through your hair and his hand tightening on your waist.

You and Dean sat in the library, chairs facing each other, kissing for several minutes. You were just thinking how you could definitely get used to this when Dean broke off the kiss and stood up. You stifled the whimper of protest you felt rising in your throat and sat back in your chair. You stared up at the hunter, sure you had done something wrong.

“Y/N...” he started to say, but you cut him off.

“I did something wrong, didn’t I?” you blurted out. Flustered, you put your face in your hands and refused to look at him.

“No,” he said, dropping to his knees in front of you. “No, you didn’t.” He pulled your hands away from your face. “I was going to ask you...I don’t want to pressure you, but, well, sitting in these hard, wooden chairs and kissing isn’t so great, so I was going to ask you if you wanted to go somewhere more comfortable. I don’t know, to my room or something.”

Shocked, you could only nod weakly. When you noticed that Dean looked skeptical, you stood up and took his hand. “That’d be great,” you said nervously.

“Are you sure?” he asked.

“Yes, I’m positive,” you answered, trying to control the tremor in your voice.

Dean took your hand, leading you out of the library and down the hallway. He stopped in front of his closed door and looked at you one more time. You nodded at him, earning yourself a smile in return as he pushed open the door. He led you to the bed, where he dropped to it with a sigh, still holding your hand.

You stood at the edge of the bed, between Dean’s legs, not sure what you should do. He put both hands on your waist and stared up at you. You leaned over and carefully kissed him on the corner of his mouth. His smiled widened and then he was pulling you onto the bed beside him, lying you next to him, his arms around you and your legs tangled together.

You felt stiff and awkward, and Dean must have sensed it. “Relax,” he said. “We won’t do anything you don’t want to, I promise.” He kissed the end of your nose and then he was kissing you again and it was amazing. He tasted like the whiskey he’d been drinking and the mint gum he chewed and he smelled fantastic, like soap and leather and something that could only be described as Dean. It wasn’t long before you relaxed and just let yourself go, enjoying the feel of his arms around you and his lips on yours.

The two of you kissed for a long time, and it was fantastic, better than you’d ever thought it could be. You found yourself wanting more. Feeling brave, you pulled away from Dean and sat up.

He laid back with a sigh. “You okay?” he asked.

You nodded as you grabbed the edge of your t-shirt and pulled it over your head, tossing it to the floor. When you looked back at Dean, his mouth was hanging open and he looked confused. You leaned over him and tugged at his t-shirt, forcing him to sit up so you could pull it off and drop it to the floor as well.

“Y/N, what are you doing?” he said.

At Dean’s words, your bravery seemed to slip away and you felt shy all over again. “I...I wanted...to, you know, try some other stuff...stuff besides, you know, kissing,” you stammered. You were sure that Dean was about to laugh you right out of his room. You couldn’t believe you’d just told him that.  While the kissing had been great, you didn’t think someone with Dean’s experience would want to do more than that with you.

But instead of throwing you out, Dean pulled you back down beside him, his warm hands running up and down your back.

“Really?” he asked incredulously.

“Yes,” you murmured. “I’m sure.”

Dean put his hand on the back of your head, pulling you to him so he could capture your lips with his. With his other hand, he expertly unhooked your bra and slid the straps down your arms, trapping it between your bodies. You shuddered, not from cold, but from nerves. Dean kissed you until you relaxed, then he pulled your bra the rest of the way off and tossed it to the floor. He moved his attentions to your neck, gently kissing his way down your throat. His hand rubbed gentle circles up your side until he reached your breast. When his thumb brushed across the nipple, you jumped, startled.

“It’s okay, Y/N,” he murmured against your throat.  “I won’t hurt you, I promise.”

You took a deep breath and nodded, trying to relax. Dean returned to his exploration of your neck, eventually moving down your body and then he was taking your breast in his mouth, suckling the nipple. Your back arched involuntarily, wanting more. He pulled you closer, gently caressing you with his hands and his mouth. The feel of his hands on you, his mouth doing things to you like you’d never felt before was overwhelming. A moan slipped past your lips.

“Mm,” Dean hummed, returning to your mouth. He kissed you and you could feel the smile on his face. He brushed a hand through your hair, raining kisses across your face and neck. His hand slid down your body and then his fingers were dancing lightly over your core, still covered by your shorts and panties.

“Dean…,” you breathed.

“Do you want me to stop?” he asked.

“No,” you sighed, shaking your head. “No, please don’t.”

Dean nodded, his hand skimming along the edge of your shorts and then he was sliding it past the waistband of your clothes and brushing his fingers across your folds. Very gently, he slipped a single finger into your dampening entrance, moving very slowly, taking his time, trying to make you comfortable.

You were so nervous, you could feel yourself trembling under Dean’s hands. He seemed to understand, because he was murmuring gentle words as he kissed you. And whatever he was doing with his hands, it was making you squirm deliciously.

You pressed yourself against Dean, silently begging him for more. You moaned again as another finger pushed into you and he rubbed his thumb across your clit. His fingers crooked and suddenly, your vision went white as pure pleasure burst through you and you were gripping Dean’s arm as the waves of sensation rushed over you.

He kissed you as you came down from the most unbelievable thing you’d ever experienced. He pulled your shorts and underwear off, adding them to the pile of clothes on the floor. Then he pushed his pajama pants off and he was nestled between your legs, kissing you some more. You could feel his arousal pressing against your leg and you were suddenly more nervous than you’d ever felt in your life. But you didn’t have to worry, because Dean was more considerate than you had ever imagined. He continued kissing you and opening you up, his touches tender and easy. It was only when he knew you were ready that he positioned himself at your entrance, his forehead resting against yours.

He kissed you as he entered you, pushing past the final barrier so carefully that you only felt a slight pinch and then he was moving inside you, his impressive length stretching you as he began slowly thrusting. He led you, showing you exactly how and when to move, patient and understanding with your lack of experience, not seeming to mind at all. Soon, you were moving together like you’d been together forever and then you were coming again, a warmth spreading through your body, filling you. Dean followed right behind you with a satisfied sigh.

He collapsed to the bed beside you, rolling to his back. “Wow,” he breathed.

You rolled to your side and looked at him, leaning on your hand. His eyes were closed and he had that familiar, self-satisfied grin on his face. You poked him in the chest with your finger and you fully expected the teasing to start.

Instead, he turned to look at you, also leaning on his hand. He stroked his thumb across your cheek before kissing you. He pulled away, leaving you breathless. “You okay?” he asked and you could see the concern in his eyes.

“I’m perfect,” you sighed. “That was...that was perfect.” And it was perfect, so much better than you imagined your first time would be. You couldn’t have asked for anything, or anyone, better.

“Yeah?” he grinned. “Good.” He laid back down and pulled you down to lie across his chest. His fingers traced lazy circles on your naked back. You were just starting to fall asleep, when you heard Dean’s voice, so quiet it was barely audible.

“I thought it was perfect, too,” he whispered, then gently kissed the top of your head.


End file.
